The compound 6-aminonorepinephrine .2HBr is disclosed in a paper by Mannich and Berger, Archiv. Pharmazie, 277, 117 (1939). It was prepared by catalytic hydrogenation of the keto moiety of the corresponding 6-amino acetophenone compound.
Immobilization of catecholamines on aryl or alkyl amine glass beads via diazotization has been described by Venter et al. in Proc. Nat. Acad. Sci., U.S.A., 69, 1141 (1972) and in Proc. Nat. Acad. Scie., U.S.A., 70, 1214 (1973).
Regeneration of solid carrier supports which have been linked to a protein material such as an enzyme, through a diazo linkage, using sodium dithionite is disclosed in German Pat. No. 2,336,428. After the regeneration, the solid carrier contains an amino group which can be used to recouple with fresh protein.